Tag: fling

FFS this post is delayed. Though unintended I have taken 2.5 months to get this sucker out…As such, here’s a little #TBT for your Thursday afternoon….

It was an ordinary November afternoon when I received a Snapchat message from good ole’ Boston Boy (upgraded to Boston Babe), my super sweet fling from the summer who took me to baseball games and held my hand at the dinner table. It said: “Hey, do you know any good places to eat in downtown Toronto?” I laughed to myself, realizing that this was exactly how he’d started our very first tinder convo (yes, I have that good a memory). I was in the middle of a drrrry spell…one that actually started when B-Boy left Toronto back in August. Work was out of control busy, I was studying for a grad school entrance exam, and had a general apathy toward dating of any kind, so ya, I didn’t hesitate setting up our date.

We agreed to meet at his hotel and I showed up nervous and excited. After all, I hadn’t seen the guy in almost 3 months and couldn’t even remember if I thought he was cute. He ended up getting stuck at work so I decided to make the best of the situation and grabbed a glass of wine and a seat at the bar. I ended up chatting to the guy at the stool next to me (don’t get the wrong idea, he was well over 50) and had a pretty hilarious time. I felt a little like the star of my own version of “Pretty Woman”, trying to set up a client while waiting for another to arrive. The gentleman asked if I was staying in the hotel, to which I replied: “Nope just visiting a friend” just as Boston Babe showed up, looking way cuter than I remembered I may add. I struggled to find my credit card and pay for the drink only looking up when the bartender yelled “THAT WAS THE SMOOTHEST THING I’VE EVER SEEN”. Always considerate, my Boston Babe had subtly paid the tab and grabbed my stuff. All I could do was muster a quiet “thank you” and grab his hand before heading straight for the elevators.

The rest of the night was honestly amazing. We hooked up, ate pizza in bed, hot-tubbed, hooked up, watched a movie, slept, and again hooked up. It was as if we picked up right where we let off and quickly transitioned from ‘what’ve you been up to’ pleasantries to meaningful conversation. I left the next morning, after enjoying a complimentary hotel breakfast, feeling elated and excited to see him again. Oh! and I mustn’t forget that the gentleman from the bar the night before turned up again, this time sitting across from me as I ate toast and scrambled eggs, while I kept my blushing cheeks pointed to my plate.

Fast forward a few weeks and I am in a full-on ‘fling-lationship’. I dub this term to explain the otherwise uncategorically expressed phenomenon: I was 100% in a relationship for a very defined period of time. We texted, ate meals together, talked about our days, and spent a lot of time together. By the last week of his trip I had definitely grown attached, more than to just having someone in my life but to him as well. We went skating one night and as he held my hands and skated backwards, guiding us around the rink I couldn’t help but think: “Why does he have to leeeeaaaveeee”. I was so happy to continue doing what we were doing that I couldn’t help but feel slighted to have found someone I get along with so well when he happens to live in another country. A country with a president like Trump no less.

We had some very deep life chats over the course of a couple weeks, even getting into our pasts and relationship deal breakers which is something I rarely share with my male companions. I admitted mine is overemotional guys…ya, I’m pretty callous…hence my hesitance to share. It turned out I needn’t worry, as his exes always complained that he didn’t open up and was too emotionally reserved…Well no wonder we friggen got along so well! I don’t like to talk about feelings with the guy I’m dating and he doesn’t like to talk about feelings. period.

Well, while our mutual fear of intimacy made for a perfect fling, it also made it kind of hard to understand if the feelings I was developing were real. By the end of his trip my mind had turned into a broken record “Should I say how I feel? Could he feel the same way? Am I asking to be rejected by a guy who admittedly doesn’t open up??” I continued this one-woman game of ‘relationship chicken’, torn between taking a risk or letting this great guy just pass me by until it was suddenly our last night together and I still hadn’t said anything. You’d think I’d be capable of uttering a simple “Hey, I like you and I’d actually give this a shot…what do you think?”, but I just couldn’t bring myself to do it.

Despite my overwhelming cowardice we had a great night. Well, no…Let me clarify. I had a perfectly good night but he was clearly VERY off…to this day I don’t know what was wrong but he didn’t enjoy the physical part of our relationship in the same way he had throughout all the time we’d spent together prior. Maybe he was also playing relationship chicken and was more wrapped up in his thoughts than in my embrace? Maybe he had a rough day at work? Who knows. I

left the next morning knowing that it’d be the last time I saw him. Whether or not he felt the way I did one thing was clear: neither of us had the balls to turn this into anything real and without someone stepping up to the plate we’d go down in history as the greatest potential relationship never to reach the major leagues.

We had a great time together and while losing him stung a bit, I was over it after a couple days and quickly dove back into work, studying and not giving a fuck about dating. I won’t be the type of girl always at someone else’s beck and call, so if he ever came back to T.O., single or not, our fling-lationship would remain safely where it belongs: on my blog.

I originally was writing this as a 2-part tale about one crazy week of my life. However, due to circumstances you can read about below, this story extends past one week. So if you need a refresher you can find Part 1 here.

Wow, you’re back! Ok… uhm, I really wasn’t expecting this!

JK I knew you’d be back. Reading my posts is like passing by a car accident: it’s a damn mess but you can’t bring yourself to look away.

Now, where were we? Oh yes. I had recently hooked up with King of the Douchelords and was feeling pretty low. So I did what every girl does when her self-esteem is reeling…I looked for validation elsewhere. Now don’t you worry my friends, I am acutely aware of how dangerous this can be, we’ve all been in the situation where you’ll settle for anyone just to get some attention. So instead of hitting up an ex or another potential fkboi, I turned to an option who seemed like the anti-douchelord: Boston Boy.

He had been messaging me consistently since our first date, making me feel pretty rotten for not giving him the time of day when he seemed like a great guy. I invited him over the following Sunday, this time to hang out in a park outside my building. It may sound dramatic but I was a little “traumatized” by the incident with King Douchlord two days prior (Part 1), and that combined with our very meh hookup was enough motivation to try keep him away from my bedroom. He didn’t seem to mind though and we spent all afternoon lying in the sun, chatting and sharing (more than) a couple of kisses. It was really sweet and exactly what I needed: time spent with a decent guy who I didn’t feel any sort of pressure to be with…he was heading back to Boston in 4 days after all.

The following night, while home watching Bachelor in Paradise (#NoRagrets), he suggested coming over and I hesitantly agreed. I wasn’t down for another hookup that would leave me feeling anything but satisfied, but thankfully he did not disappoint. Our second hookup was significantly better than the first and it seems like he’d figured out how to use what (little) the good lord had given him. We hung out again the next night…I know, I know! 3 days in a row…take a chill pill amirite? He was leaving in two days anyway and we were having a lot of fun so it didn’t feel like normal rules applied.

I was glad I’d decided to give this fling a second chance, especially because this particular type works for me. When one person is local and the other is visiting it seems like the perfect opportunity for a successful fling as you can essentially do whatever you want without feeling like anything needs to be defined. The finish line is crystal clear from the get-go and for me and so many of my friends, the expectation of where something may lead is what mentally fucks with us the most. Between this guy and my love affair in Banff, I’m beginning to think I may be a spring fling queen.

It’s actually really interesting if you think about it. I am the most successful with relationships when I don’t need to worry about the end game. Is this evidence that I self-sabotage by prematurely assessing how something will pan out or does it say something more general about modern dating? When we stop the bullshit, stop the games and just get to know the person we’re interested in, it’s pretty easy to build an awesome connection. Conversely, when you add all that “who texted who first” crapola, it ruins everything. I saw Boston Boy 3 days in a friggen row…and yes, that is a little excessive, but I can’t even imagine doing that if he wasn’t going to be disappearing at the end of it all. #FlingLyfe has shown me that being honest with someone and just acting on what feels natural is the best way to experience something that’s enjoyable and stress-free. Sure, that seems intuitive…but try it in practice I dare you! It is WAY harder to act easy and breezy when you’re planning baby names in the back of your mind during a third date.

As usual I digress, and I’m sure you’re curious to hear how this whole thing played out. I was supposed to see him one more time before he left on Thursday and was happy to tie up my fling with a neat little bow. Well you know what they say about life right? It’s what happens when you’re busy making plans. His job got extended by a week giving us more opportunity to hang out and I saw him a number of times over the next week. Hell, my roommate’s boyfriend even met him.

Fast-forward to last night, I was set to see him once more as he left for Boston today, our 2-week fling-iversary #romancegoals. We met at his hotel and bar-hopped around the city sampling craft beers and apps for the next 5 hours. I’m not going to lie, after how awkwardly things had ended with my fling in Banff, I was nervous as to how my exit would go. Well, I’m happy to report that we have a fantastic night together and I left the hotel this morning with a kiss goodbye, my watch on my wrist (see Monsieur Formidable for reference) and zero awkwardness! He said he’d look me up if he was in town again and I was cool with that. I would also be cool if he didn’t look me up, but eh, that’s for Future Samantha to decide.

After discussing my night with Miranda this morning, she said she was surprised at how easily I could separate the emotional from the physical as I did spend a significant amount of time with this guy. I guess it must be because I was never really into him in that way. We got along great and feeling intimate with someone is generally nice, so it never felt like I had to separate my emotions, they just didn’t exist. I doubt that I would have continued hooking up with Boston Boy if he was local but that’s the beauty of this stage of life. We can make self-serving decisions, take risks and try things we wouldn’t otherwise all for the sake of having new experiences, both good and bad. All I can say is that the past 2 weeks have been a friggen whirlwind and that I’ve learned more about myself and relationships in 14 days than I have in the last couple of months. Baby steps people, baby steps.